Triethylammonium formate → (2S, 3S)-3-benzoylamino-1-chloro-2-hydroxy-4phenylbutane

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Reaction Steps

(3S)-3-Benzoylamino-1-chloro-4-phenyl-2-butanone (301.8 mg, 1.0 mmol) and a formic acid/triethylamine azeotropic mixture (0.2 ml) were added to a solution of chloro(pentamethylcyclopentadienyl)rhodium (III) (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.67 mg, 0.001 mmol, s/c=1000) in ethyl acetate (0.5 ml), followed by stirring at room temperature for 2 hours. Quantitative analysis by HPLC revealed production of a desired compound, (2S, 3S)-3-benzoylamino-1-chloro-2-hydroxy-4-phenylbutane (295.6 mg; yield: 97.3%). The production ratio of the desired (2S,3S)-form to the isomeric (2R,3S)-form, (2S,3S):(2R,3S), was 22.6:1. The results of elementary analysis were as follows.

Provenance & Evidence